Building Greece Island Itinerary for April

While Milos meets all your wishes you have identified the logistical problem. Even in high season the connection mostly runs way late. Island hopping while it sounds like fun can use up valuable vacation time.
I would suggest you find an island close to Mykonos with a short ferry commute. I would suggest Naxos which is less than an hour ferry commute. It has beaches, a lovely main town with old back alleys, a Venetian era Kastro and a large waterfront promenade. It also has mountain villages where you will see what Greece used to be like. Throw in some antiquities and you have a full package.

You could also consider Paros which is similar to Naxos.

On the other hand since you are early season Santorini is also a viable option. Everything will be up and running but the tourist hoards will not be there yet. You probably could not choose a better time from a crowd perspective.

Here is Naxos
Naxos town https://www.flickr.com/photos/stanbr54/albums/72157632094558042
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689

Naxos 2019 https://www.flickr.com/photos/stanbr54/albums/72157711294807761

and Santorini https://www.flickr.com/photos/stanbr54/albums/72157632154800782

A full day in Athens likely won't be enough unless you've been there previously or unless antiquities don't interest you. You could go back to Athens for the 3-4 nights and do a day trip to one of the Saronic Islands. BTW, Porto Rafti is a quaint, picturesque little beach town near Athens airport.

Our main purpose for the trip is to spend time on the Islands. We really only have an interest in seeing the Acropolis sites, wandering Plaka (staying here), and going to the Monastiraki market. We will be landing around 4pm on the 27th and will be leaving the morning of the 29th. It feels like the right length of time for just a glimpse since we have other interests.

I too would recommend that you consider Naxos. Loved our time there; spent a day with Nicolas at Naxos Discovery Tours; easy flight back to Athens.

Two nights and a full day will certainly give you a feel for Athens. FYI - the only island I've been to is Santorini. It's definitely worth visiting! We stayed in Oia for three nights in April 2016 - spectacular views and not crowded except for sunset viewing (overrated) and the one morning a cruise ship was in port. I rented a car so we drove around the island and visited the archeological site at Akrotiri as well as the nearby Red Beach (pebbly but an awesome setting). Later we drove over to the black resort style beach at Perissa and pretty well had island and the beaches to ourselves that day. We didn't spend much time in Fira because it didn't look as pristine as the rest of the places we saw. Regardless of which island in addition to Mykonos that you visit - don't waste a lot of time on the ferry. Have a great trip!

I would agree with stanbr’s suggestions. We did enjoy Santorini for a few nights but felt it was not the Greek experience we expected. Our best experience in the Cyclades was our 6 nights on Naxos. Naxos ticked all the boxes for history, wonderful landscapes, quaint villages, excellent cuisine & wines. We would return in a heartbeat. Naxos could be a great addition to your stay on Mykonos. I can’t speak to the March/April time frame because we were there in September. We took the ferry from Athens to
Naxos>Santorini and flew back to Athens.

Greetings,
Santorini is the diamond of ALL the Greek isles and you are defiantly missing out if you do not go there. It has
ton more of your boxes checked than Mykonos. I would highly recommend you forgo your free stay with friends on Mykonos in leu of Santorini. While the beaches might be better on Mykonos there is no possible way you will be sitting on any beach or go in water for that matter in March. During season, Mykonos is known as "party capital" with their GATED, SUPER HIGH CLASS all inclusive mega resorts that European millionaires flock to(this is why the island has notoriety compared to any of the others).
With that said. You are correct. this is "OFF" season that means all the quaint cafes and shops you are dreaming about will most likely be closed on Mykonos or Santorini for that matter. Plus, better hope it is not extremely windy and cold as season dictates so you can sit at your cafe's if you find one open. Easter week April 17th 2022 is the beginning of when things start to open up on the Greek Isles.

People dislike Santorini because of the cruise ships and hoards of arrogant, loud, pushy passengers clogging the streets(just like NYC ;) ). Off season there "should" be none of that. Defiantly better chance of at least some things be open compared to Mykonos. Think of Santorini as "Niagara Falls" or "Las Vegas" a MUST SEE (wonder of the world) at least once in your life and Mykonos as simply another of the many Greek islands that tend to blend together no matter which one you pick. Good Luck!

Hi Danny,
The thing about Santorini that does not get mentioned often enough is its proximity to Folegandros, an isle that so far, has a good balance of commercial tourism with wilder, more 'authentic' rural agricultural. Folegandros has an exceptionally attractive Hora, VG cove beaches, a public bus (???) plus a local taxi, not to mention a wide variety of good restaurants plus one of the Cyclades' best-value splurge hotels.
One gets from Santorini over to Folegandros by boat.

Btw, travel writer Jennifer Barclay's latest book, Wild Abandon, gives a good description of some of the most obscure and less-trodden Dodecanese isles. Worth a read.

I am done. The end.